This article provides the first comprehensive reconstruction and analysis of Hintikka’s attempt to obtain a measure of the information yield of deductive inferences. The reconstruction is detailed by necessity due to the originality of Hintikka’s contribution. The analysis will turn out to be destructive. It dismisses Hintikka’s distinction between surface information and depth information as being of any utility towards obtaining a measure of the information yield of deductive inferences. Hintikka is right to identify the failure of canonical information theory to give an account of the information yield of deductions as a scandal, however this article demonstrates that his attempt to provide such an account fails. It fails primarily because it applies to only a restricted set of deductions in the polyadic predicate calculus, and fails to apply at all to the deductions in the monadic predicate calculus and the propositional calculus. Some corollaries of these facts are a number of undesirable and counterintuitive results concerning the proposed relation of linguistic meaning (and hence synonymy) with surface information. Some of these results will be seen to contradict Hintikka’s stated aims, whilst others are seen to be false. The consequence is that the problem of obtaining a measure of the information yield of deductive inferences remains an open one. The failure of Hintikka’s proposal will suggest that a purely syntactic approach to the problem be abandoned in favour of an intrinsically semantic one.